Potassium Carbonate → HCID 11555326, compound

HRID 20537Notes

Reaction equation

HRID 20537 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Si]([O:14][CH2:15][C@H:16]([CH3:36])[O:17][C:18]1[CH:19]=[C:20]([CH:32]=[C:33]([OH:35])[CH:34]=1)[C:21]([NH:23][C:24]1[CH:28]=[CH:27][N:26]([CH:29]([CH3:31])[CH3:30])[N:25]=1)=[O:22])(C(C)(C)C)(C)C.[Cl:37][C:38]1[CH:39]=[C:40]([CH:47]=[CH:48][C:49]=1F)[C:41]([N:43]1[CH2:46][CH2:45][CH2:44]1)=[O:42]>C(#N)C>[N:43]1([C:41]([C:40]2[CH:47]=[CH:48][C:49]([O:35][C:33]3[CH:32]=[C:20]([CH:19]=[C:18]([O:17][C@@H:16]([CH3:36])[CH2:15][OH:14])[CH:34]=3)[C:21]([NH:23][C:24]3[CH:28]=[CH:27][N:26]([CH:29]([CH3:30])[CH3:31])[N:25]=3)=[O:22])=[C:38]([Cl:37])[CH:39]=2)=[O:42])[CH2:46][CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 536296483-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]benzamideHCID 59346868(Azetidin-1-yl)(3-chloro-4-fluorophenyl)methanone

Product 1

HCID 11555326HCID 11555326, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

Potassium carbonate (182 mg, 1.32 mmol) was added to a mixture of 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxy-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide (350 mg, 0.81 mmol) and 1-(3-Chloro-4-fluorobenzoyl)azetidine (181 mg, 0.85 mmol) in acetonitrile (5 mL) and the stirred mixture heated at 160° C. in a ‘Smith Creator Microwave’ for 15 hours. The mixture was allowed to reach ambient temperature and pressure and reduced in vacuo. The residual oil was partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate layer was separated, washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (331 mg)

Workup

  1. customto reach ambient temperature
  2. customThe residual oil was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas chromatographed on silica
  8. washeluting with a gradient of 50-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-21e1992f9276478baa18bc0885628bbc
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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